5-(Trifluoromethyl)isoxazole → HCID 14280193, compound

HRID 1607905Notes

Reaction equation

HRID 1607905 reaction equation
[Na].[F:2][C:3]([F:10])([F:9])[C:4]1O[N:7]=[CH:6][CH:5]=1.[Br-].[Cl:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([Cl:23])[C:14]=1[N:24]([C:26](=O)[C:27]([F:30])([F:29])[F:28])[NH2:25]>C(O)C>[C:6]([C:5]1[C:4]([C:3]([F:10])([F:9])[F:2])=[N:25][N:24]([C:14]2[C:13]([Cl:12])=[CH:18][C:17]([C:19]([F:22])([F:21])[F:20])=[CH:16][C:15]=2[Cl:23])[C:26]=1[C:27]([F:30])([F:29])[F:28])#[N:7]

Participants

5

Reactant 3

HCID 44639815-(Trifluoromethyl)isoxazoleHCID 5360545SodiumHCID 19849800HCID 19849800, compound

Product 1

HCID 14280193HCID 14280193, compoundYield 9.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.92 g (0.04 mol) of sodium is dissolved in 25 ml of ethanol, 5.48 g (0.04 mol) of 5-trifluoromethylisoxazole are added at 0° C. and the mixture is stirred at room temperature for 15 minutes. 16.16 g (0.04 mol) of N-(2,6-dichloro-4-trifluoromethylphenyl)-trifluoroacetohydrazide bromide are added dropwise to this mixture, while cooling, and the mixtureis subsequently stirred at 25° C. for a further 10 hours. After the sodium bromide which has precipitated out is filtered off, the filtrate isconcentrated and the residue is separatad by column chromatography. 1.65 g (9.3% of theory) of 4-cyano-3,5-di(trifluoromethyl)-1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazole of melting point 88° C.-92° C. are obtained.

Workup

  1. temperaturewhile cooling
  2. stirringthe mixtureis subsequently stirred at 25° C. for a further 10 hours
  3. customAfter the sodium bromide which has precipitated out
  4. filtrationis filtered off

Sources & evidence

ORD record
ord-f9be40d72b89460e8bbf19c63f0c6b9d
Source dataset
uspto-grants-1989_09
Patent number
US04868198

Reaction notes

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